Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00477164" target="_blank" >RIV/61388963:_____/17:00477164 - isvavai.cz</a>

Výsledek na webu

<a href="https://link.springer.com/article/10.1007%2Fs11224-017-0938-7" target="_blank" >https://link.springer.com/article/10.1007%2Fs11224-017-0938-7</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11224-017-0938-7" target="_blank" >10.1007/s11224-017-0938-7</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives

Popis výsledku v původním jazyce

Classical and reverse substituent effects were studied for pyrrole derivatives. Two extensive sets of pyrrole derivatives with NO, NO2, CN, CF3, COMe, COOH, CHO, CONH2, Cl, SH, SiH3, F, PH2, H, Me, OMe, OH, NH2, NHMe, NMe2, Li, BeH, BH2, Na, MgH, and AlH2 substituents at N and C3 positions were taken into account. Analysis of the substituent effects was based on charges of the Substituent Active Region (cSAR). The cSAR values were obtained from atomic charges calculated within the Quantum Theory of Atoms in Molecules (QTAIM) methodology. Calculations were performed at the B3LYP/6-311++G** level of theory. It was documented that classical substituent effect in substituted pyrroles is much greater (approximately ten times) for substituents at C3 position than at NH group. The reverse substituent effect is also greater in C3-substituted pyrroles that in N-substituted ones. As a result of observed correlations, substituent constants for some rare substituents such as Li, BeH, BH2, Na, MgH, and AlH2 were evaluated.

Název v anglickém jazyce

Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives

Popis výsledku anglicky

Classical and reverse substituent effects were studied for pyrrole derivatives. Two extensive sets of pyrrole derivatives with NO, NO2, CN, CF3, COMe, COOH, CHO, CONH2, Cl, SH, SiH3, F, PH2, H, Me, OMe, OH, NH2, NHMe, NMe2, Li, BeH, BH2, Na, MgH, and AlH2 substituents at N and C3 positions were taken into account. Analysis of the substituent effects was based on charges of the Substituent Active Region (cSAR). The cSAR values were obtained from atomic charges calculated within the Quantum Theory of Atoms in Molecules (QTAIM) methodology. Calculations were performed at the B3LYP/6-311++G** level of theory. It was documented that classical substituent effect in substituted pyrroles is much greater (approximately ten times) for substituents at C3 position than at NH group. The reverse substituent effect is also greater in C3-substituted pyrroles that in N-substituted ones. As a result of observed correlations, substituent constants for some rare substituents such as Li, BeH, BH2, Na, MgH, and AlH2 were evaluated.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Structural Chemistry

ISSN

1040-0400

e-ISSN

—

Svazek periodika

28

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

5

Strana od-do

1223-1227

Kód UT WoS článku

000404241800028

EID výsledku v databázi Scopus

2-s2.0-85014752744